Method of handling and storing gasoline containing lecithin



F HANDLING AND sronmooaso METHOD LINE CONTAINING LECITHIN Endre F. Sipos, Decatur, and Donald E. Sincroft, Fort Company, Inc.,

Wayne, Iud., assignors to' Central Soya Fort Wayne, Ind., a corporation of'Indiana No Drawing. Filed Feb. 13, 1959, Ser. No. 792,946

.. 10 Claims. (Cl. 44-.-66).

This invention relates to a method of handling and storing gasoline containing lecithin.

It has heretofore been proposed that lecithin be added to gasoline for the purpose of eliminating carburetor and intake manifold deposits, de-icing, rust control, and other benefits, as described more particularly in our copending application Serial No. 695,540, filed November 12., 1957.. For such applications, only very minute quantities of the lecithin are required, such as 50 p.p.m., but even such minute amounts of lecithin have been found to create a problem. in the handling and storage of the gasoline. These undesirable side effects appear to be generally related to the so-called bacterial spoilage of gasoline. The reason why the presence, of a few parts per million of lecithin in. gasoline tends to promote the .bacteri-alspoilage of the gasoline is not understood. However, it has been observed that the problem is particularly acute when the gasoline containing the lecithin is stored in tanks containing a water bottom which is contaminated with bacteria and other microorganisms which attack the gasoline at the interface between the water and the gasoline. Since the use of water layers in gasoline storage tanks is a common practice in order to insure against the loss of the gasoline by leakage, it can be seen that the problem is of considerable magnitude and requiresa solution before the beneficial effects of adding lecithin to gasoline can be fully obtained.

It is therefore a general object of the present invention to provide an improved method of handling and storing gasoline containing lecithin. A more specific object is to provide a means for counteracting the tendency of the lecithin to promote bacterial spoilage of the gasoline. Further objects and advantages will appear as the specification proceeds.

In one of the preferred embodiments of the present invention, an alkyl boronic acid is incorporated in the gasoline in a suflicient amount to overcome the tendency of the lecithin therein to promote bacterial spoilage. For example, with gasolines containing from 5 to 500 p.p.m. of lecithin, from 0.1 to 100 p.p.m. of an alkyl boronic acid can be introduced into the gasoline in accordance with the present invention. Where the gasoline contains at least 50 p.p.m. of lecithin, it Will usually be desirable to employ at least 1 p.p.m. of the alkyl boronic acid. However, it will usually not be necessary to employ more than parts of the alkyl boronic acid in order to substantially eliminate the tendency of the lecithin to promote bacterial spoilage.

The action of the alkyl boronic acids is not fully understood. However, it appears to be related to the relative solubility of the compounds in water and gasoline. Alkyl boronic acids containing from 4 to 12 carbon atoms are believed to be particularly suitable. Compounds of this class are elfective in overcoming the tendency of the lecithin to promote bacterial spoilage, while at the same time contributing other desirable properties to the gasoline. Among the specific compounds in this group which can be mentioned are n-hexyl boronic acid, n-octyl boronic acid, 2-ethyl hexyl boronic acid, n-butyl boronic acid, nonyl boronic acid, and duodecyl boronic acid. Such compounds are preferably used in the amounts described above.

The term lecithin as used in this application is intended to refer to thecommercial grades of lecithin which. are obtained from vegetable oils, such, as soybean oil.. Such lecithin materials are obtained by a centrifugal sepa--' ration from crude soybean oil, etc., and dried toa-low.

, value.

- Patented .July 4, 1 961.

moisture value, and filtered to a low. benzene-insoluble to; as vegetable oil phosphatides, since they containmixtures of phosphatidic substances. The term lecithin however, has become accepted as the common name-of such products, and is so used in this application. The. phosphatidic components of the lecithin are. normally chemically unmodified from the stage in which they nat-, urally occur in vegetable oils. 7 The term gasoline as used herein is intended torefer to those fractions of petroleum hydrocarbons which are commonly employed as fuels for internal combustion engines. Such petroleum hydrocarbon fractions haveconsiderably lesser density than water, and can be floated on a water layer in a storage tank.

As a specific example of the method of practicing the present invention, a filtered lecithin product obtained from soybean oil is dissolved in a commercial gasoline in the amount of approximately p.p.m. To the same gasoline is; added n-octyl boronic acid in the amount of 10 p.p.m. The gasolineis then ready for'dist'ribution; through the channels of commerce. The problem of bacterial spoilage during the handling and storage of the gasoline will have been minimized, and the gasoline can be safely stored in tanks having a water layer in the bottom thereof even though the water layer is contaminated with bacteria and other microorganisms. The gasoline would simply be pumped into the tank in the regular way, and would float on top of the water layer. Normally the volume of gasoline in such tank would greatly exceed the volume of the water layer.

As a further specific example, 50 p.p.m. of a soybean phosphatidic material (e.g. commercial lecithin) is incorporated in a commercial gasoline together with 1 p.p.m. of Z-ethyl hexyl boronic acid. The gasoline is then ready for handling and storage in the manner previously described.

In either of the above examples, comparable amounts of other alkyl boronic acids can be substituted, such as n-hexyl boronic acid, n-butyl boronic acid, duo-decyl boronic acid, etc.

While the use of the alkyl boronic acids as described above is preferred, it is to be understood that certain other organoboron compounds can be employed with some degree of success in accordance with the present invention. Instead of the alkyl 'boronic acids, alkyl borates or alkyl borines can be used. In some cases, the boron compound can be heterocyclic. For example, borazoles can be used. It will be understood from the foregoing that the organoboron compounds should be used in a sufiicient amount to overcome the tendency of the lecithin to promote the bacterial spoilage of the gasoline. Among the heterocyclic boron compounds which have some value in connection with the present invention are N-tris (2-propyl) borazole, N-tris (2-propyl) -B-tris (dimethylamino) borazole, and N-tris (2-propyl) -B-trimethyl-borazole. These specific compounds are illustrative of the general class of borazoles referred to above. Borinate esters can also be used, such as nbutyl di-n-butylborinate, methyl diphenylborinate, ethyl diphenylborinate isobutyl diphenylborinate, n-butyl di-ptolylborinate, methyl di-n-butylborinate, phenyl dipropylborinate, and methyl di-t-butylborinate.

While in the foregoing specification the present invention has been described in relation to specific embodiments thereof, it will be understood that the invention is susceptible to other embodiments and that many of the Such lecithin materials, have also been referred,

details described herein can be varied without departing H V 2. The method of claim 1 wherein said alkyl boronic:

acid is n-hexyl boronic acid.

3. The method of claim 1 wherein said alkyl boronic acid is n-octyl boronic acid.

4. The method of claim 1 wherein said alkyl'boronic acid is Z-ethyl hexyl boronic acid.

5; In the handling and storage of gasoline containing at least 50 and up to around 500 p.p.m. of lecithin, the improvement comprising combining with said gasoline at least 1 p.p.m. and up to p.p.m. of an alkyl boronic acid containing from 4 to 12 carbon atoms.

6. The improved method of storing gasoline containing from 5 to 500 p.p.m. of lecithin, comprising incorporating in said gasoline from 0.1 to 100 p.p.m. of an alkyl boronic acid containing from 4 to 12 carbon atoms, and thereafter introducing the gasoline containing said lecithin and said alkyl boronic acid into a storage tank having a water layer in the bottom thereof.

7. The improved method of storing gasoline containing at least 50 and up to around 500 p.p.m. of lecithin, comprising incorporating in said gasoline from 1 to 10 p.p.m. of an alkyl boronic acid containing from 4 to 12 carbon atoms, and thereafter introducing the gasoline containing said lecithin and said alkyl boronic acid into a storage tank having a water layer in the bottom thereof.

8. The method of claim 7 in which said alkyl boronic acid is n-hexyl boronic acid.

9. The method of claim 7 in which said alkyl boronic acid is n-octyl boronic acid.

10. The method of claim 7 in which said alkyl boronic 10 acid is 2-ethyl hexyl boronic acid.

References Cited in the file of this patent UNITED STATES PATENTS Rees et a1. July 11, 1939 2,208,105 'Ratltbun July 16, 1940 2,322,007 Fischer June 15, 1943 2,352,760 Bell July 4, 1944 2,402,590 Arnold June 25,1946

2,680,058 Harris et a1. June 1, 1954 2,710,251 Darling June 7,1955

FOREIGN PATENTS 776,314 Great Britain June 5, 1957' OTHER REFERENCES Uses and Applications of Chemicals and Related Mapage 47. 

1. IN THE HANDLING AND STORAGE OF GASOLINE CONTAINING FROM 5 TO 500 P.P.M. OF LECITHIN, THE IMPROVEMENT COMPRISING ALSO INCORPORATING IN SAID GASOLINE FROM 0.1 TO 100 P.P.M. OF AN ALKYL BORONIC ACID CONTAINING FROM 4 TO 12 CARBON ATOMS. 